It happened at the height of the boom. Ask Jeeves bought our company for over $500 million. As part of the acquisition I and many others were awarded with a hefty pile of stock options, but those options were locked up for a year or so in order to encourage us to stay at the new company. On paper, at the time of the acquisition, my stock options were worth well over $1 million, and the stock price of Jeeves was somewhere around $110.

By the time I could exercise my stock options a year later they were worth under $10,000 and the company stock price was under $1. We were lucky to survive the bubble burst…

Prior to all that it was pretty amazing. Our startup had a game room with pinball, pool, ping pong, etc. and we’d regularly have major discussions while playing a game. The company also bought us lunch every Friday for the better part of two years. And we had a really amazing team of engineers & leaders running the place. I’ve kept in touch with a number of those folks over the years, and have a number of those connections to thank for more than one job I’ve held after that one.